Trifluoroacetic acid → 4-{[2-(3,5-Difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine

HRID 2180169

반응식

HRID 2180169 반응식
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][NH:22][C:23](=[O:33])[CH2:24][C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=2)([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:31][C:29]1[CH:30]=[C:25]([CH2:24][C:23]([NH:22][CH2:21][C:11]2([C:14]3[CH:15]=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:33])[CH:26]=[C:27]([F:32])[CH:28]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 685306044-{[2-(3,5-Difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 224903764-{[2-(3,5-Difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-{[2-(3,5-difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.09 g, 0.16 mmol) in CH2Cl2 (1.5 mL) at 0° C. was added TFA (0.5 mL, to give a 25% v/v solution). The mixture was stirred at room temperature for 3 h at which time TLC (4:1 hexanes/EtOAc) showed no starting material left. The solvent was removed by rotary evaporation and the resulting liquid was evaporated from toluene (2×10 mL) then diluted with EtOAc (100 mL) and washed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated by rotary evaporation, and dried under high vacuum for 1 h to yield 4-{[2-(3,5-difluoro-phenyl)-acetylamino]-methyl}-4-(4-iodo-phenyl)-piperidine as a reddish solid (0.038 g, ˜0.08 mmol). MS (ESI): 471.1 (M+1).

후처리

  1. customto give a 25% v/v solution)
  2. waitleft
  3. customThe solvent was removed by rotary evaporation
  4. customthe resulting liquid was evaporated from toluene (2×10 mL)
  5. additionthen diluted with EtOAc (100 mL)
  6. washwashed with 10% aqueous NaHCO3 solution (2×50 mL) and saturated brine (50 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customdried under high vacuum for 1 h

출처 및 근거

ORD 기록
ord-8ea325c2608e4ee583544cfda3cfcb56
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887889B2

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